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Introduction:

It was an overcast and mild day in mid-June many years ago and I was just nineteen. I was staying at my uncle’s farm to help him out a bit as well as take a little time to figure out my plans for the future. Job, schooling, career, girls, and fun all had to be considered...

It was an overcast and mild day in mid-June many years ago and I was just nineteen. I was staying at my uncle’s farm to help him out a bit as well as take a little time to figure out my plans for the future. Job, schooling, career, girls, and fun all had to be considered in the decisions I soon needed to make. Finding contemplating such things was best done in the outdoors I spent a lot of my free time hiking around the area’s scattered woods and scrub brush festooned rolling hillsides. This particular day I’d been stomping around for hours and it seemed the farther I went the more lost in thought I became. Suddenly I snapped out of it and realized I had become rather disoriented. I couldn’t say I was lost though because I could still see the hill in the distance with the distinctive rock outcropping that bordered the farm. I just had to kind of bushwhack my way down to the road I knew went through the shallow valley below me. I wasn’t familiar with this stretch of land but knew I’d be ok now.

Scrambling cross-country down the uneven slope I made my way through a tangled grove of stunted trees to find myself confronted by an old weathered fence. I could see the back of a sign attached to it and was curious about what it said. After climbing the fence I read the sign and got a most unpleasant feeling in the pit of my stomach. In bold letters it nearly screamed, NO TRESPASSING KEEP OUT.

Oops!, I thought as I sheepishly turned to walk the remaining distance to the road. I hadn’t gone more than fifty yards when I heard a distinctive and unmistakable sound, the sound of a gun being cocked!

“We take a dim view of trespassers around here son. Turn around and put your hands up!” a raspy masculine voice commanded firmly. Terrified, I thought my thumping heart would pound right out of my chest! I did as the voice said and faced my captor. Turning, I faced a stocky man in his fifties wearing grubby clothes and pointing a rifle at me.

“Get walking that way.” he said gesturing with his gun. And I did. “We’re going to my house to call the sheriff! Now move!” he barked gruffly. “I …I’m sorry, I didn’t mean to trespass sir! I was kind of lost.” I desperately tried to explain.

“Just keep goin.” is all I heard from him. Then I saw the old, dingy, little house with a few scattered out buildings clustered around it. Trying to console myself any way possible I thought, “Well, if he’s calling the sheriff at least he’s not likely to be a serial killer.”

Arriving at the door of the rustic dwelling my “host” said “Go in, it’s not locked.” As expected it was cluttered and unkempt with a lot of antiquated furnishings mixed with some modern conveniences. I stood in the center of a fairly large living room as he stood by the door and closed it behind him. His next words left me in shock, “Take off your shoes and socks, then your shorts and undies and toss them over here. I want to see your ass.” My heart was really thumping again when I peeled off running shorts and dropped my briefs to floor. Then I bent over, scooped them up and tossed them over to him. This was as good as tying me up since I couldn’t escape bottomless!

With that he reached for the phone and started dialing. He told the sheriff he’d caught a trespasser and then he started whispering so low I couldn’t make out what was being said. Then he hung up. “He’s in the area and will be here shortly.” he told me.

Again I desperately pleaded my case that my trespassing had been unintentional and expressed how sorry I was. But it again had no effect and I could just as well have been talking to a wall. How could I get out of this?

Then I heard a vehicle pull up and park. So did my host who went and opened the door to let the officer in. Still facing away from them I glanced back to see what he looked like. He was a very imposing figure decked out in his uniform and was at least six foot three.

“God! You were right! That IS a great ass!” the officer gushed. What? I thought to myself. “Got something for lube?” he asked the host. “Yeah, lots.” came the reply. With my host ahead of me and the sheriff behind me I was escorted to a bedroom. On seeing it had a bathroom I begged to use it and they let me. As I was in there I heard them moving around doing stuff. When I came out I was shocked to see both of them were stark NAKED! “What the hell was going on?!” I wondered.

My host then spoke up and said, “Alright kid, here’s the deal. We can make this whole mess go away, forget we ever saw you, and even drop you off where you want to go but we each get to have our way with that cute ass of yours. If not, I press charges, there’s jail, and a bad mark on your record forever. What’s it gonna be?” The gears in my brain cranked at full speed trying to process the situation.

“Uh, what do you mean by “have your way” exactly?” I asked nervously.

“Simple kid, we each take a turn sticking our dick in your ass and fucking you like a girl any way we want. And by the way, we’re going to record it and play it back so you can watch yourself getting fucked.“

My jaw dropped. The thought of actually being penetrated by another male had never entered my brain! Were they serious?! They sure seemed to be. My mind raced to find any possible way out of this but could find none. I knew law enforcement was extremely sparse in this county and the only one available for miles wanted to screw my butt! My uncle had no clue I was here and I couldn’t afford legal trouble. I had no choice.

Defeated I hung my head and mumbled “ok.”

My host smiled and said “Great, kneel on the bed with your butt and feet over the edge. You’ll like it, I guarantee. “Still wearing my T shirt but naked below the waist I climbed onto the bed and got in position. I overheard, “Hand me the lube before you pick up the camera. Thanks.” I felt like a fort that was about to be overrun by an invading army. All of my defenses were down.

Hands started roaming over my body, especially my butt. A finger started at my lower back and slowly ran down the deepening cleft between my cheeks. They were slowly pulled apart and a voice said “Wow! Look at this beautiful hole! Let’s see how it feels.” Then came a brief pause and the sudden shocking realization that something long and narrow was being pushed into my butt. I knew it had to be his finger when his knuckles touched me. “Is this the first thing you’ve ever had in there?” he asked probing inside me. “Yeah.” I admitted.

“Ah, so you are a virgin just like I thought. Like it?” he probed with both meanings of the word equally appropriate in my situation. “Uh, yeah.”

“Good.” And I felt his digit leave my rear.

A moment later I heard, “There, that should be plenty. You filmin? Make sure you get his face and my dick going into him.” The sheriff’s voice “Recording, go ahead. “

This was NOT happening! It couldn’t be happening! My thoughts screamed. But it was. This line of thought was shattered as I felt the slick, rubbery, head enter between my cheeks and press firmly against the last holdout of my virginity. “Don’t fight it, just let it in.”

I tried, and it started gradually making progress. The pressure was starting to get a bit painful when my body gave in and I blurted an involuntary “OH MY GOD!!!” as he buried his cock in my bottom! His hands gripped my hips and the shaft started thrusting within me. I was appalled at what was happening to me but the sensations of his member rubbing against my soft rectal walls were sublime!

“He likes it, you should see the look on his face! How does he feel in there?” the sheriff said as I caught a glimpse of his naked, hairy, legs a couple feet from my head. “Might be the best butt hole I’ve ever fucked! You’re gonna love being in him!” came the enthusiastic reply.

The thrusting was becoming more and more frantic and I heard “OH! I.. !... I’m CUMMING! “then I felt his fluid squirting inside me. I heard “Get a close up of it coming out.”

Moments later he pulled out of me and I suddenly felt empty. I knew that would not last long. But I was relieved and had actually, enjoyed how it had felt. I thought to myself that maybe I would be ok.

“Well, he’s all warmed up for ya Bill. Hand me the camera. Thanks, ready when you are.” I heard as I tried to figure out if I should move or not. “Kid, all I did was break you in a little, now you’re gonna get seriously FUCKED! Bill loves to fuck ass and you’re just the kind of boy he likes, young, smooth, and slender. That’s really why I called him. He can make a boy feel real good! He’s all yours Bill. How do you want him?”

In his deep base voice Bill said “Climb on the bed Kid. I want to show you something.” Still wearing just my T shirt I laid on the bed and for the first time sized up Bill. He was I his forties, about six foot three well -muscled, hairy, had dark hair and a mustache. But his COCK! I hadn’t really paid much attention to it earlier, probably because it was still soft. Now it was at least eight inches long with bulging greenish veins and topped by a plump helmet shaped tip already oozing a trickle of clear fluid. It stood out boldly from a dense tangled nest of dark pubic hair. I tried desperately to not think of what he clearly intended to do with it.

Joining me on the bed and getting on his knees Bill asked ”Ever handle another guy’s cock? Go ahead, put your hands on it.” I touched it and then started exploring the mighty shaft of carnal flesh. My hand grasped it and felt its firmness. I marveled at the heft of his testicles and the softness of the bulging head. He squirted a big glob of lube onto it and had me slather it all over his cock. When I finished the other guy handed me a towel to wipe my hands on. At Bill’s instruction I reclined on my back and brought my knees clear back to my chest. This completely laid bare my newly deflowered butt hole and boy parts.

“WOW! That’s the most beautiful boy butt I’ve ever seen! Are ya filmin? I’m gonna see how deep I can get in this boy.” Bill said as he placed the head of his cock at my entrance. “Breathe deep and think happy thoughts boy, it’ll make this easier.”

The tip started pressing hard against my orifice but it resisted gallantly. The invader retreated and tried again over and over and each time gained a little more ground as I stretched ever wider. Breathing deeply I let my mind go as I closed my eyes and thought of hiking through the countryside. After just a moment or two of this I was jolted back to reality when the rubbery tip lurched suddenly through my little anus. I gasped but the pain of this challenging intromission was manageable. Now past the most intimidating and uncomfortable phase, Bill’s stately penis glided smoothly into my most intimate depths. Indescribable pleasures emanated from its passage and it’s rubbing against my delicate rectal walls. It just kept going, sinking deeper and deeper. Finally it stopped and I felt Bill’s hairy bush and ball sack push against me. Bill was now fully entrenched in my hairless little bottom! And it felt… it felt…… well, GOOD!

“Good job son, I knew you could take it! Your butt feels SO GOOD! Now I’m gonna fuck you in your boy hole!” With this I opened my eyes to see his face right above me with my ankles resting on his broad shoulders. His statement was not idle chatter and he immediately started pumping in and out of me and it felt even better!

This had all been so intense I had lost track of anything else going on beyond the pleasures of my own body. Becoming more aware of things I noticed the other guy standing nearby with the camera in his hands apparently filming Bill’s cock fucking me and I was actually glad since I was curious what this all looked like. He fucked me hard in this position for a long time then told me he wanted to see my butt as he fucked me.

He had me kneel on my hands and knees with my legs kind of bent then he knelt upright behind me. With little effort his organ reentered my butt as his big hands grasped my hips. Bill’s powerful body thumped hard against my buttocks and I loved the sensation of his big penis rhythmically thrusting in the hot juicy corridor of my boyish rectum. I was lost in pleasure.

The other guy laughed and said,” He likes it! He has a hard on!” Bill’s hand reached under me, found my erection and stared masturbating it. This along with the cock pumping in me was too much and I squirted my cum all over the bed. This caused my hole to repeatedly clamp down hard then release the cock inside me so intensely that Bill suddenly grunted and let loose. I could feel the gush of his semen flooding the innermost chambers of my rectum. The pulsations of his orgasmic organ ebbed and Bill slowly pulled it out of my once virginal rump. “There, now don’t tell us you didn’t like that, we know very well that you did.” Bill said as we started to clean up.

We were all exhausted but satisfied as they played back the recording for me. My curiosity was raging and I really wanted to see what it all looked like from another angle. And they had gotten it. It was amazing to see them sliding into my butt, fucking me, close-ups of my face responding to the pleasure, and graphic close-ups of their cocks pumping my butt hole. It was amazing to watch.

We got dressed and they kept their word. I got in Bill’s sheriff vehicle and we started back to my uncle’s place. I was lost in thought recalling all I had experienced that afternoon and how surprisingly good it had felt. How long would it be till I could feel that way again? The longing stirred in me getting worse and worse as we bumped along the old dirt road. “You ok?” Bill asked. “Can we do it again? Would you fuck me again now?” I asked nearly begging. “Uh, sure, I can pull over there.” We headed to small a dense grove of oak trees just off the road and went just far enough in to be out of sight. He had me bend over and brace myself against a tree trunk. He dropped my pants and a moment later his cock was buried once again in my butt. Frantically he pumped me ramming hard against my buttocks. I couldn’t get enough! All too soon he came in me but for now at least I’d had my fill, literally.

Bill dropped me off near my uncle’s entrance road and I thanked him. As I walked back up the road to the house I pondered on what this all meant. I definitely still liked girls but they couldn’t provide for these newly awakened desires.

In time I had great experiences with both guys and girls but no encounter ever seemed to match the excitement of this first time when I was caught trespassing.

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